Using the same sentence structure for all subheadings

Hi guys,

I've started to work as a digital marketing and SEO intern for an insurance company and I'm helping this company to generate SEO articles to get more visitors. The thing is even though I'm an intern, there is no one I can have a discussion with. My boss mostly tries to shape our marketing strategy. I know it sounds bad. But there is one thing that looks super annoying in our articles. He's making our writing team write the subheading of articles in this way;

Title: 5 reasons why. you need an insurance

H2: 5 reasons why you need insurance: bla bla bla

H2: 5 reasons why you need insurance: another blaa bla bla

It goes like this. I think this is all wrong and not natural. I saw the same structure in a well-ranked page and he's trying to do the same thing. I want to talk to him about this but I could not find abstract info about how wrong this is. So, What do you think? Should I really care about this kind of headings?